Sodium Bicarbonate → 1-(5-Hydroxy-6,7-dimethyl-benzofuran-2-yl)-2-morpholin-4-yl-ethanone

HRID 480981Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 480981
[CH3:1][C:2]1[C:19]([O:20]C(=O)C)=[CH:18][C:5]2[CH:6]=[C:7]([C:9](=[O:17])[CH2:10][N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[O:8][C:4]=2[C:3]=1[CH3:24].C(=O)(O)[O-].[Na+]>CO>[OH:20][C:19]1[C:2]([CH3:1])=[C:3]([CH3:24])[C:4]2[O:8][C:7]([C:9](=[O:17])[CH2:10][N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:6][C:5]=2[CH:18]=1

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 10236780Acetic acid 6,7-dimethyl-2-(2-morpholin-4-yl-acetyl)-benzofuran-5-yl ester

Produkt 1

HCID 102364101-(5-Hydroxy-6,7-dimethyl-benzofuran-2-yl)-2-morpholin-4-yl-ethanoneAusbeute 54,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of acetic acid 6,7-dimethyl-2-(2-morpholin4-yl-acetyl)-benzofuran-5-yl ester (23 mg), prepared as in Example 17, in MeOH (10 mL) was stirred while sodium bicarbonate (10 mg) was added. Then the mixture was stirred at RT overnight, followed by evaporation to dryness. The residue was purified by silica gel column, eluting with 5% MeOH in dichloromethane to give 11 mg of 1-(5-hydroxy-6,7-dimethyl-benzofuran-2-yl)-2-morpholin-4-yl-ethanone as an oil. Conversion into HCl salt gave a yellow solid. 1H NMR (CD3OD, 300 MHz) δ: 7.60 (s, 1H), 7.20 (s, 1H), 3.78 (m, 6H), 2.64 (m, 4H), 2.50 (s, 3H), 2.40 (s, 3H) ppm. 13C NMR (CDCl3, 75 MHz) δ: 187.98, 170.20, 153.31, 152.29, 146.58, 130.44, 124.53, 122.80, 114.36, 113.15, 64.69, 53.79, 21.28, 13.47, 12.86 ppm. M/S 290 (M+H+).

Aufarbeitung

  1. additionwas added
  2. customfollowed by evaporation to dryness
  3. customThe residue was purified by silica gel column
  4. washeluting with 5% MeOH in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-0342f01a9fa946ce88315252eda02b97
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06653346B1

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